# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_bodipyh

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H44 B2 F4 N6 O2'
_chemical_formula_sum            'C44 H44 B2 F4 N6 O2'
_chemical_formula_weight         786.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.4702(6)
_cell_length_b                   13.1470(6)
_cell_length_c                   14.9642(8)
_cell_angle_alpha                113.625(4)
_cell_angle_beta                 95.348(4)
_cell_angle_gamma                105.167(4)
_cell_volume                     1944.74(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    18532
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.43

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed Tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_method       'rotation method'
_diffrn_measurement_details      
; 209 frames, detector distance = 70 mm
;
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19662
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_sigmaI/netI    0.0928
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.23
_reflns_number_total             9507
_reflns_number_gt                5494
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SAINT (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1030P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9507
_refine_ls_number_parameters     525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_obs         0.1536
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4299(2) 0.61212(18) 0.65481(16) 0.0321(4) Uani 1 1 d . . .
H1 H 0.3427 0.5882 0.6320 0.038 Uiso 1 1 calc R . .
C2 C 0.49269(19) 0.53383(17) 0.62840(15) 0.0297(4) Uani 1 1 d . . .
N3 N 0.44330(16) 0.41249(14) 0.57100(13) 0.0315(4) Uani 1 1 d . . .
B4 B 0.3086(2) 0.3362(2) 0.54385(19) 0.0331(5) Uani 1 1 d . . .
N5 N 0.30673(17) 0.20653(15) 0.47547(14) 0.0347(4) Uani 1 1 d . . .
C6 C 0.1944(2) 0.1239(2) 0.4269(2) 0.0437(6) Uani 1 1 d . . .
H6 H 0.1219 0.1459 0.4339 0.052 Uiso 1 1 calc R . .
C7 C 0.1827(2) 0.0102(2) 0.3685(2) 0.0501(6) Uani 1 1 d . . .
H7 H 0.1027 -0.0464 0.3356 0.060 Uiso 1 1 calc R . .
C8 C 0.2883(2) -0.0238(2) 0.35669(19) 0.0440(6) Uani 1 1 d . . .
H8 H 0.2809 -0.1028 0.3148 0.053 Uiso 1 1 calc R . .
C9 C 0.4026(2) 0.05916(19) 0.40668(17) 0.0359(5) Uani 1 1 d . . .
C10 C 0.41204(19) 0.17815(18) 0.46732(16) 0.0321(4) Uani 1 1 d . . .
N11 N 0.52738(16) 0.25699(15) 0.51502(13) 0.0314(4) Uani 1 1 d . . .
C12 C 0.53842(19) 0.36798(18) 0.56406(15) 0.0300(4) Uani 1 1 d . . .
C13 C 0.65678(19) 0.46352(17) 0.61901(15) 0.0300(4) Uani 1 1 d . . .
C14 C 0.62636(19) 0.56546(18) 0.65895(15) 0.0305(4) Uani 1 1 d . . .
C15 C 0.6971(2) 0.68533(18) 0.72530(16) 0.0325(4) Uani 1 1 d . . .
H15 H 0.7842 0.7094 0.7488 0.039 Uiso 1 1 calc R . .
C16 C 0.63369(19) 0.76290(17) 0.75297(15) 0.0312(4) Uani 1 1 d . . .
N17 N 0.68031(17) 0.88240(15) 0.82051(13) 0.0332(4) Uani 1 1 d . . .
B18 B 0.8092(2) 0.9506(2) 0.8845(2) 0.0388(6) Uani 1 1 d . . .
N19 N 0.80870(17) 1.07936(16) 0.95006(14) 0.0350(4) Uani 1 1 d . . .
C20 C 0.9187(2) 1.1581(2) 1.01070(18) 0.0412(5) Uani 1 1 d . . .
H20 H 0.9908 1.1352 1.0080 0.049 Uiso 1 1 calc R . .
C21 C 0.9278(2) 1.2696(2) 1.07563(19) 0.0448(6) Uani 1 1 d . . .
H21 H 1.0057 1.3238 1.1174 0.054 Uiso 1 1 calc R . .
C22 C 0.8224(2) 1.3034(2) 1.08029(18) 0.0419(5) Uani 1 1 d . . .
H22 H 0.8279 1.3808 1.1253 0.050 Uiso 1 1 calc R . .
C23 C 0.7106(2) 1.22429(19) 1.01947(17) 0.0367(5) Uani 1 1 d . . .
C24 C 0.7033(2) 1.10871(18) 0.95020(16) 0.0333(4) Uani 1 1 d . . .
N25 N 0.59101(17) 1.03313(15) 0.88984(14) 0.0337(4) Uani 1 1 d . . .
C26 C 0.5839(2) 0.92543(18) 0.83020(16) 0.0323(4) Uani 1 1 d . . .
C27 C 0.46882(19) 0.83181(18) 0.76321(15) 0.0308(4) Uani 1 1 d . . .
F28 F 0.26767(12) 0.33684(12) 0.62863(10) 0.0430(3) Uani 1 1 d . . .
F29 F 0.23060(12) 0.36658(11) 0.49205(11) 0.0421(3) Uani 1 1 d . . .
O30 O 0.51284(15) 0.04110(13) 0.40503(12) 0.0402(4) Uani 1 1 d . . .
C31 C 0.5147(2) -0.07303(18) 0.33741(18) 0.0399(5) Uani 1 1 d . . .
H31A H 0.4749 -0.0937 0.2681 0.048 Uiso 1 1 calc R . .
H31B H 0.4693 -0.1337 0.3564 0.048 Uiso 1 1 calc R . .
C32 C 0.6483(2) -0.06634(19) 0.34472(18) 0.0381(5) Uani 1 1 d . . .
H32A H 0.6825 -0.0601 0.4106 0.046 Uiso 1 1 calc R . .
H32B H 0.6962 0.0052 0.3401 0.046 Uiso 1 1 calc R . .
C33 C 0.6632(2) -0.1740(2) 0.26193(19) 0.0464(6) Uani 1 1 d . . .
H33A H 0.6184 -0.2447 0.2690 0.056 Uiso 1 1 calc R . .
H33B H 0.6240 -0.1824 0.1964 0.056 Uiso 1 1 calc R . .
C34 C 0.7963(2) -0.1692(2) 0.2621(2) 0.0453(6) Uani 1 1 d . . .
H34A H 0.8336 -0.1700 0.3241 0.054 Uiso 1 1 calc R . .
H34B H 0.8438 -0.0949 0.2615 0.054 Uiso 1 1 calc R . .
C35 C 0.8056(3) -0.2723(3) 0.1719(3) 0.0744(10) Uani 1 1 d . . .
H35A H 0.7604 -0.3458 0.1748 0.089 Uiso 1 1 calc R . .
H35B H 0.7631 -0.2735 0.1106 0.089 Uiso 1 1 calc R . .
C36 C 0.9344(3) -0.2719(3) 0.1628(2) 0.0660(8) Uani 1 1 d . . .
H36A H 0.9310 -0.3420 0.1033 0.099 Uiso 1 1 calc R . .
H36B H 0.9774 -0.2722 0.2224 0.099 Uiso 1 1 calc R . .
H36C H 0.9794 -0.2014 0.1567 0.099 Uiso 1 1 calc R . .
C37 C 0.77783(19) 0.44583(18) 0.62694(15) 0.0318(4) Uani 1 1 d . . .
C38 C 0.7865(2) 0.33722(19) 0.61608(17) 0.0361(5) Uani 1 1 d . . .
H38 H 0.7133 0.2743 0.6029 0.043 Uiso 1 1 calc R . .
C39 C 0.9010(2) 0.3211(2) 0.62437(18) 0.0410(5) Uani 1 1 d . . .
H39 H 0.9053 0.2465 0.6155 0.049 Uiso 1 1 calc R . .
C40 C 1.0089(2) 0.4118(2) 0.64538(19) 0.0435(5) Uani 1 1 d . . .
H40 H 1.0873 0.4010 0.6535 0.052 Uiso 1 1 calc R . .
C41 C 1.0009(2) 0.5188(2) 0.6544(2) 0.0451(6) Uani 1 1 d . . .
H41 H 1.0744 0.5813 0.6675 0.054 Uiso 1 1 calc R . .
C42 C 0.8878(2) 0.53549(19) 0.64470(18) 0.0376(5) Uani 1 1 d . . .
H42 H 0.8842 0.6091 0.6501 0.045 Uiso 1 1 calc R . .
F43 F 0.83877(15) 0.90466(12) 0.94887(12) 0.0547(4) Uani 1 1 d . . .
F44 F 0.89860(13) 0.95675(13) 0.82928(12) 0.0576(4) Uani 1 1 d . . .
O45 O 0.60105(15) 1.24447(13) 1.01752(12) 0.0413(4) Uani 1 1 d . . .
C46 C 0.6013(2) 1.35948(19) 1.08397(17) 0.0389(5) Uani 1 1 d . . .
H46A H 0.6568 1.4200 1.0697 0.047 Uiso 1 1 calc R . .
H46B H 0.6309 1.3765 1.1544 0.047 Uiso 1 1 calc R . .
C47 C 0.4706(2) 1.35999(19) 1.06675(18) 0.0393(5) Uani 1 1 d . . .
H47A H 0.4183 1.3056 1.0887 0.047 Uiso 1 1 calc R . .
H47B H 0.4382 1.3310 0.9942 0.047 Uiso 1 1 calc R . .
C48 C 0.4612(2) 1.48266(19) 1.12323(18) 0.0388(5) Uani 1 1 d . . .
H48A H 0.4938 1.5115 1.1957 0.047 Uiso 1 1 calc R . .
H48B H 0.5138 1.5369 1.1013 0.047 Uiso 1 1 calc R . .
C49 C 0.3298(2) 1.4847(2) 1.10664(18) 0.0425(5) Uani 1 1 d . . .
H49A H 0.2798 1.4375 1.1357 0.051 Uiso 1 1 calc R . .
H49B H 0.2940 1.4468 1.0338 0.051 Uiso 1 1 calc R . .
C50 C 0.3194(2) 1.6071(2) 1.1520(2) 0.0453(6) Uani 1 1 d . . .
H50A H 0.3511 1.6439 1.2253 0.054 Uiso 1 1 calc R . .
H50B H 0.3721 1.6557 1.1253 0.054 Uiso 1 1 calc R . .
C51 C 0.1879(3) 1.6065(3) 1.1300(2) 0.0584(7) Uani 1 1 d . . .
H51A H 0.1552 1.5684 1.0574 0.088 Uiso 1 1 calc R . .
H51B H 0.1868 1.6876 1.1580 0.088 Uiso 1 1 calc R . .
H51C H 0.1363 1.5633 1.1604 0.088 Uiso 1 1 calc R . .
C52 C 0.34628(19) 0.84431(17) 0.75097(16) 0.0307(4) Uani 1 1 d . . .
C53 C 0.3096(2) 0.92187(19) 0.83015(17) 0.0355(5) Uani 1 1 d . . .
H53 H 0.3663 0.9705 0.8930 0.043 Uiso 1 1 calc R . .
C54 C 0.1907(2) 0.9276(2) 0.81684(18) 0.0395(5) Uani 1 1 d . . .
H54 H 0.1667 0.9804 0.8708 0.047 Uiso 1 1 calc R . .
C55 C 0.1063(2) 0.8573(2) 0.72602(18) 0.0392(5) Uani 1 1 d . . .
H55 H 0.0241 0.8599 0.7183 0.047 Uiso 1 1 calc R . .
C56 C 0.1432(2) 0.7830(2) 0.64630(18) 0.0376(5) Uani 1 1 d . . .
H56 H 0.0866 0.7361 0.5832 0.045 Uiso 1 1 calc R . .
C57 C 0.2618(2) 0.77709(18) 0.65838(16) 0.0327(4) Uani 1 1 d . . .
H57 H 0.2864 0.7268 0.6031 0.039 Uiso 1 1 calc R . .
C58 C 0.50157(19) 0.73228(18) 0.71854(16) 0.0311(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.360(3) . ?
C1 C58 1.431(3) . ?
C1 H1 0.9500 . ?
C2 N3 1.393(3) . ?
C2 C14 1.455(3) . ?
N3 C12 1.360(3) . ?
N3 B4 1.518(3) . ?
B4 F29 1.366(3) . ?
B4 F28 1.391(3) . ?
B4 N5 1.591(3) . ?
N5 C6 1.353(3) . ?
N5 C10 1.356(3) . ?
C6 C7 1.357(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 O30 1.346(3) . ?
C9 C10 1.428(3) . ?
C10 N11 1.359(3) . ?
N11 C12 1.308(3) . ?
C12 C13 1.473(3) . ?
C13 C14 1.384(3) . ?
C13 C37 1.468(3) . ?
C14 C15 1.433(3) . ?
C15 C16 1.359(3) . ?
C15 H15 0.9500 . ?
C16 N17 1.401(3) . ?
C16 C58 1.447(3) . ?
N17 C26 1.362(3) . ?
N17 B18 1.504(3) . ?
B18 F44 1.381(3) . ?
B18 F43 1.385(3) . ?
B18 N19 1.583(3) . ?
N19 C20 1.355(3) . ?
N19 C24 1.362(3) . ?
C20 C21 1.365(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9500 . ?
C23 O45 1.350(3) . ?
C23 C24 1.430(3) . ?
C24 N25 1.362(3) . ?
N25 C26 1.312(3) . ?
C26 C27 1.475(3) . ?
C27 C58 1.380(3) . ?
C27 C52 1.460(3) . ?
O30 C31 1.442(2) . ?
C31 C32 1.503(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.526(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.511(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.518(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.495(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C42 1.400(3) . ?
C37 C38 1.402(3) . ?
C38 C39 1.387(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.381(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.387(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.376(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
O45 C46 1.438(2) . ?
C46 C47 1.500(3) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.530(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.514(3) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.519(3) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.511(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C57 1.400(3) . ?
C52 C53 1.404(3) . ?
C53 C54 1.385(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.385(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.391(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.383(3) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C58 116.81(19) . . ?
C2 C1 H1 121.6 . . ?
C58 C1 H1 121.6 . . ?
C1 C2 N3 127.42(19) . . ?
C1 C2 C14 124.14(19) . . ?
N3 C2 C14 108.43(17) . . ?
C12 N3 C2 108.05(17) . . ?
C12 N3 B4 122.77(17) . . ?
C2 N3 B4 127.27(17) . . ?
F29 B4 F28 109.61(18) . . ?
F29 B4 N3 113.62(19) . . ?
F28 B4 N3 111.04(19) . . ?
F29 B4 N5 109.29(18) . . ?
F28 B4 N5 108.01(18) . . ?
N3 B4 N5 105.04(17) . . ?
C6 N5 C10 120.81(19) . . ?
C6 N5 B4 116.97(18) . . ?
C10 N5 B4 122.20(17) . . ?
N5 C6 C7 121.5(2) . . ?
N5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O30 C9 C8 126.5(2) . . ?
O30 C9 C10 113.71(18) . . ?
C8 C9 C10 119.8(2) . . ?
N5 C10 N11 123.51(18) . . ?
N5 C10 C9 118.93(19) . . ?
N11 C10 C9 117.55(19) . . ?
C12 N11 C10 118.31(18) . . ?
N11 C12 N3 125.35(19) . . ?
N11 C12 C13 124.65(18) . . ?
N3 C12 C13 109.99(17) . . ?
C14 C13 C37 130.30(19) . . ?
C14 C13 C12 105.60(17) . . ?
C37 C13 C12 124.10(17) . . ?
C13 C14 C15 133.20(19) . . ?
C13 C14 C2 107.93(18) . . ?
C15 C14 C2 118.71(18) . . ?
C16 C15 C14 116.9(2) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 N17 127.6(2) . . ?
C15 C16 C58 124.26(19) . . ?
N17 C16 C58 108.07(17) . . ?
C26 N17 C16 108.20(17) . . ?
C26 N17 B18 123.80(17) . . ?
C16 N17 B18 127.42(18) . . ?
F44 B18 F43 109.6(2) . . ?
F44 B18 N17 113.1(2) . . ?
F43 B18 N17 111.4(2) . . ?
F44 B18 N19 108.6(2) . . ?
F43 B18 N19 107.98(19) . . ?
N17 B18 N19 106.02(17) . . ?
C20 N19 C24 121.45(19) . . ?
C20 N19 B18 116.01(18) . . ?
C24 N19 B18 122.45(18) . . ?
N19 C20 C21 121.3(2) . . ?
N19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 119.6(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 119.6(2) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
O45 C23 C22 125.8(2) . . ?
O45 C23 C24 114.18(19) . . ?
C22 C23 C24 120.0(2) . . ?
N19 C24 N25 123.59(19) . . ?
N19 C24 C23 118.02(19) . . ?
N25 C24 C23 118.37(19) . . ?
C26 N25 C24 117.95(18) . . ?
N25 C26 N17 125.76(19) . . ?
N25 C26 C27 124.74(18) . . ?
N17 C26 C27 109.50(17) . . ?
C58 C27 C52 128.39(19) . . ?
C58 C27 C26 105.71(18) . . ?
C52 C27 C26 125.88(18) . . ?
C9 O30 C31 118.07(17) . . ?
O30 C31 C32 107.09(18) . . ?
O30 C31 H31A 110.3 . . ?
C32 C31 H31A 110.3 . . ?
O30 C31 H31B 110.3 . . ?
C32 C31 H31B 110.3 . . ?
H31A C31 H31B 108.6 . . ?
C31 C32 C33 111.67(19) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 C33 C32 114.1(2) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 111.5(2) . . ?
C33 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C36 C35 C34 115.4(3) . . ?
C36 C35 H35A 108.4 . . ?
C34 C35 H35A 108.4 . . ?
C36 C35 H35B 108.4 . . ?
C34 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C42 C37 C38 117.81(19) . . ?
C42 C37 C13 121.61(19) . . ?
C38 C37 C13 120.58(19) . . ?
C39 C38 C37 120.4(2) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C40 C39 C38 121.0(2) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C39 C40 C41 118.9(2) . . ?
C39 C40 H40 120.6 . . ?
C41 C40 H40 120.6 . . ?
C42 C41 C40 120.8(2) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C37 121.0(2) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
C23 O45 C46 117.40(18) . . ?
O45 C46 C47 107.13(18) . . ?
O45 C46 H46A 110.3 . . ?
C47 C46 H46A 110.3 . . ?
O45 C46 H46B 110.3 . . ?
C47 C46 H46B 110.3 . . ?
H46A C46 H46B 108.5 . . ?
C46 C47 C48 112.19(19) . . ?
C46 C47 H47A 109.2 . . ?
C48 C47 H47A 109.2 . . ?
C46 C47 H47B 109.2 . . ?
C48 C47 H47B 109.2 . . ?
H47A C47 H47B 107.9 . . ?
C49 C48 C47 112.86(19) . . ?
C49 C48 H48A 109.0 . . ?
C47 C48 H48A 109.0 . . ?
C49 C48 H48B 109.0 . . ?
C47 C48 H48B 109.0 . . ?
H48A C48 H48B 107.8 . . ?
C48 C49 C50 114.0(2) . . ?
C48 C49 H49A 108.7 . . ?
C50 C49 H49A 108.7 . . ?
C48 C49 H49B 108.7 . . ?
C50 C49 H49B 108.7 . . ?
H49A C49 H49B 107.6 . . ?
C51 C50 C49 112.7(2) . . ?
C51 C50 H50A 109.1 . . ?
C49 C50 H50A 109.1 . . ?
C51 C50 H50B 109.1 . . ?
C49 C50 H50B 109.1 . . ?
H50A C50 H50B 107.8 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C57 C52 C53 118.43(19) . . ?
C57 C52 C27 119.77(18) . . ?
C53 C52 C27 121.80(19) . . ?
C54 C53 C52 120.1(2) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 121.0(2) . . ?
C55 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C54 C55 C56 119.2(2) . . ?
C54 C55 H55 120.4 . . ?
C56 C55 H55 120.4 . . ?
C57 C56 C55 120.3(2) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C56 C57 C52 120.8(2) . . ?
C56 C57 H57 119.6 . . ?
C52 C57 H57 119.6 . . ?
C27 C58 C1 132.3(2) . . ?
C27 C58 C16 108.45(18) . . ?
C1 C58 C16 119.07(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C58 C1 C2 N3 177.1(2) . . . . ?
C58 C1 C2 C14 -1.5(3) . . . . ?
C1 C2 N3 C12 -179.1(2) . . . . ?
C14 C2 N3 C12 -0.3(2) . . . . ?
C1 C2 N3 B4 -14.7(4) . . . . ?
C14 C2 N3 B4 164.1(2) . . . . ?
C12 N3 B4 F29 -138.5(2) . . . . ?
C2 N3 B4 F29 59.2(3) . . . . ?
C12 N3 B4 F28 97.4(2) . . . . ?
C2 N3 B4 F28 -64.9(3) . . . . ?
C12 N3 B4 N5 -19.1(3) . . . . ?
C2 N3 B4 N5 178.57(19) . . . . ?
F29 B4 N5 C6 -46.8(3) . . . . ?
F28 B4 N5 C6 72.4(3) . . . . ?
N3 B4 N5 C6 -169.0(2) . . . . ?
F29 B4 N5 C10 134.7(2) . . . . ?
F28 B4 N5 C10 -106.1(2) . . . . ?
N3 B4 N5 C10 12.5(3) . . . . ?
C10 N5 C6 C7 -0.1(4) . . . . ?
B4 N5 C6 C7 -178.6(2) . . . . ?
N5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 O30 178.8(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C6 N5 C10 N11 -179.3(2) . . . . ?
B4 N5 C10 N11 -0.9(3) . . . . ?
C6 N5 C10 C9 -0.2(3) . . . . ?
B4 N5 C10 C9 178.25(19) . . . . ?
O30 C9 C10 N5 -179.31(19) . . . . ?
C8 C9 C10 N5 1.0(3) . . . . ?
O30 C9 C10 N11 -0.1(3) . . . . ?
C8 C9 C10 N11 -179.8(2) . . . . ?
N5 C10 N11 C12 -6.4(3) . . . . ?
C9 C10 N11 C12 174.4(2) . . . . ?
C10 N11 C12 N3 -0.6(3) . . . . ?
C10 N11 C12 C13 -179.80(19) . . . . ?
C2 N3 C12 N11 -179.4(2) . . . . ?
B4 N3 C12 N11 15.4(3) . . . . ?
C2 N3 C12 C13 -0.1(2) . . . . ?
B4 N3 C12 C13 -165.37(19) . . . . ?
N11 C12 C13 C14 179.8(2) . . . . ?
N3 C12 C13 C14 0.5(2) . . . . ?
N11 C12 C13 C37 -1.0(3) . . . . ?
N3 C12 C13 C37 179.76(19) . . . . ?
C37 C13 C14 C15 -4.7(4) . . . . ?
C12 C13 C14 C15 174.6(2) . . . . ?
C37 C13 C14 C2 -179.9(2) . . . . ?
C12 C13 C14 C2 -0.7(2) . . . . ?
C1 C2 C14 C13 179.4(2) . . . . ?
N3 C2 C14 C13 0.6(2) . . . . ?
C1 C2 C14 C15 3.4(3) . . . . ?
N3 C2 C14 C15 -175.39(18) . . . . ?
C13 C14 C15 C16 -176.8(2) . . . . ?
C2 C14 C15 C16 -2.0(3) . . . . ?
C14 C15 C16 N17 176.4(2) . . . . ?
C14 C15 C16 C58 -1.1(3) . . . . ?
C15 C16 N17 C26 -176.8(2) . . . . ?
C58 C16 N17 C26 1.0(2) . . . . ?
C15 C16 N17 B18 -5.4(4) . . . . ?
C58 C16 N17 B18 172.4(2) . . . . ?
C26 N17 B18 F44 -125.8(2) . . . . ?
C16 N17 B18 F44 64.0(3) . . . . ?
C26 N17 B18 F43 110.3(2) . . . . ?
C16 N17 B18 F43 -59.9(3) . . . . ?
C26 N17 B18 N19 -6.9(3) . . . . ?
C16 N17 B18 N19 -177.1(2) . . . . ?
F44 B18 N19 C20 -55.3(3) . . . . ?
F43 B18 N19 C20 63.5(3) . . . . ?
N17 B18 N19 C20 -177.0(2) . . . . ?
F44 B18 N19 C24 128.2(2) . . . . ?
F43 B18 N19 C24 -113.0(2) . . . . ?
N17 B18 N19 C24 6.4(3) . . . . ?
C24 N19 C20 C21 1.1(4) . . . . ?
B18 N19 C20 C21 -175.5(2) . . . . ?
N19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 O45 178.7(2) . . . . ?
C21 C22 C23 C24 -1.4(4) . . . . ?
C20 N19 C24 N25 179.2(2) . . . . ?
B18 N19 C24 N25 -4.5(3) . . . . ?
C20 N19 C24 C23 -2.5(3) . . . . ?
B18 N19 C24 C23 173.8(2) . . . . ?
O45 C23 C24 N19 -177.4(2) . . . . ?
C22 C23 C24 N19 2.7(3) . . . . ?
O45 C23 C24 N25 1.0(3) . . . . ?
C22 C23 C24 N25 -178.9(2) . . . . ?
N19 C24 N25 C26 1.7(3) . . . . ?
C23 C24 N25 C26 -176.6(2) . . . . ?
C24 N25 C26 N17 -2.2(3) . . . . ?
C24 N25 C26 C27 177.5(2) . . . . ?
C16 N17 C26 N25 177.4(2) . . . . ?
B18 N17 C26 N25 5.6(4) . . . . ?
C16 N17 C26 C27 -2.3(2) . . . . ?
B18 N17 C26 C27 -174.2(2) . . . . ?
N25 C26 C27 C58 -176.9(2) . . . . ?
N17 C26 C27 C58 2.9(2) . . . . ?
N25 C26 C27 C52 1.4(3) . . . . ?
N17 C26 C27 C52 -178.8(2) . . . . ?
C8 C9 O30 C31 6.4(3) . . . . ?
C10 C9 O30 C31 -173.25(19) . . . . ?
C9 O30 C31 C32 175.63(19) . . . . ?
O30 C31 C32 C33 -168.7(2) . . . . ?
C31 C32 C33 C34 176.9(2) . . . . ?
C32 C33 C34 C35 -174.1(3) . . . . ?
C33 C34 C35 C36 177.1(3) . . . . ?
C14 C13 C37 C42 -25.7(4) . . . . ?
C12 C13 C37 C42 155.2(2) . . . . ?
C14 C13 C37 C38 154.8(2) . . . . ?
C12 C13 C37 C38 -24.3(3) . . . . ?
C42 C37 C38 C39 1.0(3) . . . . ?
C13 C37 C38 C39 -179.5(2) . . . . ?
C37 C38 C39 C40 1.3(4) . . . . ?
C38 C39 C40 C41 -2.4(4) . . . . ?
C39 C40 C41 C42 1.3(4) . . . . ?
C40 C41 C42 C37 1.0(4) . . . . ?
C38 C37 C42 C41 -2.1(3) . . . . ?
C13 C37 C42 C41 178.4(2) . . . . ?
C22 C23 O45 C46 0.9(3) . . . . ?
C24 C23 O45 C46 -179.0(2) . . . . ?
C23 O45 C46 C47 179.3(2) . . . . ?
O45 C46 C47 C48 -172.46(19) . . . . ?
C46 C47 C48 C49 180.0(2) . . . . ?
C47 C48 C49 C50 -173.4(2) . . . . ?
C48 C49 C50 C51 177.4(2) . . . . ?
C58 C27 C52 C57 -33.6(3) . . . . ?
C26 C27 C52 C57 148.4(2) . . . . ?
C58 C27 C52 C53 145.9(2) . . . . ?
C26 C27 C52 C53 -32.0(3) . . . . ?
C57 C52 C53 C54 2.3(3) . . . . ?
C27 C52 C53 C54 -177.2(2) . . . . ?
C52 C53 C54 C55 0.1(4) . . . . ?
C53 C54 C55 C56 -2.2(4) . . . . ?
C54 C55 C56 C57 1.7(3) . . . . ?
C55 C56 C57 C52 0.8(3) . . . . ?
C53 C52 C57 C56 -2.8(3) . . . . ?
C27 C52 C57 C56 176.73(19) . . . . ?
C52 C27 C58 C1 -5.5(4) . . . . ?
C26 C27 C58 C1 172.8(2) . . . . ?
C52 C27 C58 C16 179.5(2) . . . . ?
C26 C27 C58 C16 -2.2(2) . . . . ?
C2 C1 C58 C27 -176.2(2) . . . . ?
C2 C1 C58 C16 -1.6(3) . . . . ?
C15 C16 C58 C27 178.8(2) . . . . ?
N17 C16 C58 C27 0.9(2) . . . . ?
C15 C16 C58 C1 3.0(3) . . . . ?
N17 C16 C58 C1 -174.87(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.063
_database_code_depnum_ccdc_archive 'CCDC 1003614'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_yafei

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H42 B2 F6 N6 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C46 H46 B2 Cl4 F6 N6 O2'
_chemical_formula_weight         992.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.7273(4)
_cell_length_b                   19.7110(10)
_cell_length_c                   25.1808(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.316(7)
_cell_angle_gamma                90.00
_cell_volume                     2327.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    27380
_cell_measurement_theta_min      1.77
_cell_measurement_theta_max      66.56

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    2.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2743
_exptl_absorpt_correction_T_max  0.8007
_exptl_absorpt_process_details   'STOE X-RED'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'Incoatec microSource Cu'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29347
_diffrn_reflns_av_R_equivalents  0.2707
_diffrn_reflns_av_sigmaI/netI    0.1175
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         67.98
_reflns_number_total             4141
_reflns_number_gt                1828
_reflns_threshold_expression     >2σ(I)
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.045(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4141
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2451
_refine_ls_R_factor_gt           0.1847
_refine_ls_wR_factor_ref         0.4790
_refine_ls_wR_factor_obs         0.4392
_refine_ls_goodness_of_fit_ref   1.445
_refine_ls_restrained_S_all      1.445
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0599(19) 0.6607(4) 0.5721(3) 0.072(2) Uani 1 1 d . . .
C2 C 0.092(2) 0.6155(5) 0.5509(3) 0.065(2) Uani 1 1 d . . .
C3 C 0.115(2) 0.6071(5) 0.4932(4) 0.074(3) Uani 1 1 d . A .
C4 C 0.303(2) 0.5535(5) 0.4896(3) 0.066(2) Uani 1 1 d . . .
C5 C 0.403(2) 0.5301(4) 0.5431(4) 0.064(2) Uani 1 1 d . . .
N6 N 0.2703(18) 0.5695(4) 0.5798(3) 0.072(2) Uani 1 1 d . . .
B7 B 0.300(2) 0.5631(5) 0.6406(4) 0.068(3) Uani 1 1 d . . .
N8 N 0.1368(18) 0.6267(4) 0.6599(3) 0.071(2) Uani 1 1 d . . .
C8 C 0.591(2) 0.4792(5) 0.5547(4) 0.072(3) Uani 1 1 d . . .
H8 H 0.6512 0.4658 0.5906 0.086 Uiso 1 1 calc R . .
C9 C 0.156(2) 0.6350(6) 0.7156(4) 0.080(3) Uani 1 1 d . . .
H9 H 0.2762 0.6061 0.7387 0.096 Uiso 1 1 calc R . .
C10 C 0.003(2) 0.6838(5) 0.7366(4) 0.080(3) Uani 1 1 d . . .
H10 H 0.0261 0.6912 0.7742 0.096 Uiso 1 1 calc R . .
C11 C -0.189(2) 0.7236(6) 0.7028(4) 0.081(3) Uani 1 1 d . . .
H11 H -0.3069 0.7556 0.7177 0.098 Uiso 1 1 calc R . .
C12 C -0.205(2) 0.7163(5) 0.6494(4) 0.071(2) Uani 1 1 d . . .
C13 C -0.043(2) 0.6653(5) 0.6271(3) 0.068(2) Uani 1 1 d . . .
C14 C -0.032(2) 0.6501(5) 0.4518(4) 0.073(3) Uani 1 1 d . . .
C17 C -0.303(3) 0.7339(6) 0.3714(5) 0.098(4) Uani 1 1 d . . .
C15A C -0.121(11) 0.7171(14) 0.4643(10) 0.102(13) Uani 0.49(4) 1 d P A 1
H15A H -0.0996 0.7329 0.5002 0.123 Uiso 0.49(4) 1 calc PR A 1
C16A C -0.242(8) 0.7600(18) 0.4211(13) 0.101(10) Uani 0.49(4) 1 d P A 1
H16A H -0.2793 0.8065 0.4275 0.121 Uiso 0.49(4) 1 calc PR A 1
C19A C -0.213(7) 0.6687(15) 0.3592(12) 0.078(8) Uani 0.49(4) 1 d P A 1
H19A H -0.2334 0.6534 0.3232 0.094 Uiso 0.49(4) 1 calc PR A 1
C20A C -0.095(6) 0.6273(15) 0.3995(9) 0.071(7) Uani 0.49(4) 1 d P A 1
H20A H -0.0555 0.5814 0.3915 0.086 Uiso 0.49(4) 1 calc PR A 1
C15B C -0.284(6) 0.6865(17) 0.4590(10) 0.079(8) Uani 0.51(4) 1 d P A 2
H15B H -0.3700 0.6802 0.4907 0.095 Uiso 0.51(4) 1 calc PR A 2
C16B C -0.404(8) 0.7309(15) 0.4203(10) 0.089(9) Uani 0.51(4) 1 d P A 2
H16B H -0.5566 0.7594 0.4273 0.106 Uiso 0.51(4) 1 calc PR A 2
C18B C -0.087(12) 0.701(2) 0.3621(13) 0.132(17) Uani 0.51(4) 1 d P A 2
H18B H -0.0229 0.7050 0.3279 0.158 Uiso 0.51(4) 1 calc PR A 2
C19B C 0.070(9) 0.6574(17) 0.4028(9) 0.097(12) Uani 0.51(4) 1 d P A 2
H19B H 0.2379 0.6344 0.3958 0.117 Uiso 0.51(4) 1 calc PR A 2
F20 F -0.4291(19) 0.7739(4) 0.3319(3) 0.127(3) Uani 1 1 d . A .
F21 F 0.1761(13) 0.5041(3) 0.6573(2) 0.0802(18) Uani 1 1 d . . .
F22 F 0.5818(13) 0.5651(3) 0.6636(2) 0.0790(17) Uani 1 1 d . . .
O23 O -0.3846(15) 0.7512(3) 0.6117(3) 0.0768(19) Uani 1 1 d . . .
C24 C -0.546(2) 0.8061(5) 0.6318(5) 0.083(3) Uani 1 1 d . . .
H24A H -0.4154 0.8420 0.6477 0.099 Uiso 1 1 calc R . .
H24B H -0.6586 0.7891 0.6596 0.099 Uiso 1 1 calc R . .
C25 C -0.741(3) 0.8335(6) 0.5844(5) 0.100(4) Uani 1 1 d . . .
H25A H -0.8681 0.8680 0.5972 0.120 Uiso 1 1 calc R . .
H25B H -0.8613 0.7961 0.5680 0.120 Uiso 1 1 calc R . .
C26 C -0.579(3) 0.8656(7) 0.5413(6) 0.111(4) Uani 1 1 d . . .
H26A H -0.4471 0.8319 0.5288 0.133 Uiso 1 1 calc R . .
H26B H -0.4642 0.9045 0.5568 0.133 Uiso 1 1 calc R . .
C27 C -0.796(3) 0.8904(8) 0.4928(6) 0.124(5) Uani 1 1 d . . .
H27A H -0.9126 0.8513 0.4784 0.149 Uiso 1 1 calc R . .
H27B H -0.9255 0.9242 0.5059 0.149 Uiso 1 1 calc R . .
C28 C -0.657(3) 0.9212(9) 0.4489(7) 0.135(6) Uani 1 1 d . . .
H28A H -0.5231 0.8879 0.4364 0.162 Uiso 1 1 calc R . .
H28B H -0.5447 0.9611 0.4629 0.162 Uiso 1 1 calc R . .
C29 C -0.870(5) 0.9431(15) 0.4015(8) 0.214(13) Uani 1 1 d . . .
H29A H -0.9678 0.9030 0.3850 0.321 Uiso 1 1 calc R . .
H29B H -0.7689 0.9663 0.3751 0.321 Uiso 1 1 calc R . .
H29C H -1.0101 0.9739 0.4139 0.321 Uiso 1 1 calc R . .
C1L C 0.254(5) 0.9527(11) 0.7546(8) 0.181(10) Uani 1 1 d . . .
H1L1 H 0.3889 0.9559 0.7879 0.217 Uiso 1 1 calc R . .
H1L2 H 0.0802 0.9785 0.7603 0.217 Uiso 1 1 calc R . .
Cl2L Cl 0.1648(16) 0.8719(3) 0.7441(2) 0.220(4) Uani 1 1 d . . .
Cl3L Cl 0.4034(16) 0.9898(3) 0.70425(19) 0.182(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.299(12) . ?
N1 C13 1.379(11) . ?
C2 N6 1.382(12) . ?
C2 C3 1.482(12) . ?
C3 C4 1.389(13) . ?
C3 C14 1.451(14) . ?
C4 C8 1.432(12) 3_666 ?
C4 C5 1.445(13) . ?
C5 C8 1.349(13) . ?
C5 N6 1.412(11) . ?
N6 B7 1.524(13) . ?
B7 F22 1.383(13) . ?
B7 F21 1.392(12) . ?
B7 N8 1.582(13) . ?
N8 C13 1.344(12) . ?
N8 C9 1.404(11) . ?
C8 C4 1.432(12) 3_666 ?
C8 H8 0.9500 . ?
C9 C10 1.348(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.345(13) . ?
C11 H11 0.9500 . ?
C12 O23 1.374(12) . ?
C12 C13 1.422(13) . ?
C14 C19B 1.39(2) . ?
C14 C20A 1.39(2) . ?
C14 C15B 1.42(2) . ?
C14 C15A 1.43(3) . ?
C17 C18B 1.25(4) . ?
C17 F20 1.349(13) . ?
C17 C16A 1.35(3) . ?
C17 C16B 1.38(3) . ?
C17 C19A 1.40(3) . ?
C15A C16A 1.44(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C19A C20A 1.36(4) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C15B C16B 1.38(3) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C18B C19B 1.47(4) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
O23 C24 1.450(12) . ?
C24 C25 1.511(17) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.541(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.568(19) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.486(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.52(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C1L Cl2L 1.66(2) . ?
C1L Cl3L 1.695(18) . ?
C1L H1L1 0.9900 . ?
C1L H1L2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C13 119.6(8) . . ?
N1 C2 N6 124.4(8) . . ?
N1 C2 C3 126.5(8) . . ?
N6 C2 C3 109.0(8) . . ?
C4 C3 C14 130.5(8) . . ?
C4 C3 C2 106.1(8) . . ?
C14 C3 C2 123.3(8) . . ?
C3 C4 C8 133.1(9) . 3_666 ?
C3 C4 C5 108.5(8) . . ?
C8 C4 C5 118.4(8) 3_666 . ?
C8 C5 N6 127.0(8) . . ?
C8 C5 C4 124.6(8) . . ?
N6 C5 C4 108.4(8) . . ?
C2 N6 C5 108.0(7) . . ?
C2 N6 B7 123.7(8) . . ?
C5 N6 B7 128.3(8) . . ?
F22 B7 F21 108.5(8) . . ?
F22 B7 N6 112.3(9) . . ?
F21 B7 N6 112.6(8) . . ?
F22 B7 N8 109.2(8) . . ?
F21 B7 N8 109.1(8) . . ?
N6 B7 N8 104.9(7) . . ?
C13 N8 C9 120.2(8) . . ?
C13 N8 B7 123.7(7) . . ?
C9 N8 B7 115.4(8) . . ?
C5 C8 C4 116.9(9) . 3_666 ?
C5 C8 H8 121.5 . . ?
C4 C8 H8 121.5 3_666 . ?
C10 C9 N8 120.3(10) . . ?
C10 C9 H9 119.8 . . ?
N8 C9 H9 119.8 . . ?
C9 C10 C11 119.9(9) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.8(10) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 O23 126.1(9) . . ?
C11 C12 C13 120.3(9) . . ?
O23 C12 C13 113.4(8) . . ?
N8 C13 N1 122.0(8) . . ?
N8 C13 C12 119.2(8) . . ?
N1 C13 C12 118.6(8) . . ?
C19B C14 C20A 41.2(15) . . ?
C19B C14 C15B 116.9(16) . . ?
C20A C14 C15B 101.7(16) . . ?
C19B C14 C15A 104.1(18) . . ?
C20A C14 C15A 118.3(17) . . ?
C15B C14 C15A 40.0(15) . . ?
C19B C14 C3 120.6(14) . . ?
C20A C14 C3 121.1(14) . . ?
C15B C14 C3 122.5(12) . . ?
C15A C14 C3 120.6(12) . . ?
C18B C17 F20 117.2(17) . . ?
C18B C17 C16A 107(3) . . ?
F20 C17 C16A 118.9(17) . . ?
C18B C17 C16B 122(2) . . ?
F20 C17 C16B 120.9(16) . . ?
C16A C17 C16B 41.0(15) . . ?
C18B C17 C19A 38(2) . . ?
F20 C17 C19A 119.6(16) . . ?
C16A C17 C19A 121.3(19) . . ?
C16B C17 C19A 107.8(17) . . ?
C14 C15A C16A 118(2) . . ?
C14 C15A H15A 120.8 . . ?
C16A C15A H15A 120.8 . . ?
C17 C16A C15A 120(2) . . ?
C17 C16A H16A 120.2 . . ?
C15A C16A H16A 120.2 . . ?
C20A C19A C17 120(2) . . ?
C20A C19A H19A 120.2 . . ?
C17 C19A H19A 120.2 . . ?
C19A C20A C14 122(2) . . ?
C19A C20A H20A 119.0 . . ?
C14 C20A H20A 119.0 . . ?
C16B C15B C14 120.4(19) . . ?
C16B C15B H15B 119.8 . . ?
C14 C15B H15B 119.8 . . ?
C15B C16B C17 120(2) . . ?
C15B C16B H16B 119.9 . . ?
C17 C16B H16B 119.9 . . ?
C17 C18B C19B 121(2) . . ?
C17 C18B H18B 119.3 . . ?
C19B C18B H18B 119.3 . . ?
C14 C19B C18B 119(2) . . ?
C14 C19B H19B 120.7 . . ?
C18B C19B H19B 120.7 . . ?
C12 O23 C24 116.0(7) . . ?
O23 C24 C25 106.6(9) . . ?
O23 C24 H24A 110.4 . . ?
C25 C24 H24A 110.4 . . ?
O23 C24 H24B 110.4 . . ?
C25 C24 H24B 110.4 . . ?
H24A C24 H24B 108.6 . . ?
C24 C25 C26 113.3(11) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 C27 110.0(12) . . ?
C25 C26 H26A 109.7 . . ?
C27 C26 H26A 109.7 . . ?
C25 C26 H26B 109.7 . . ?
C27 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C28 C27 C26 113.6(12) . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C27 C28 C29 112.9(13) . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28B 109.0 . . ?
C29 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl2L C1L Cl3L 114.5(9) . . ?
Cl2L C1L H1L1 108.6 . . ?
Cl3L C1L H1L1 108.6 . . ?
Cl2L C1L H1L2 108.6 . . ?
Cl3L C1L H1L2 108.6 . . ?
H1L1 C1L H1L2 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C2 N6 1.2(15) . . . . ?
C13 N1 C2 C3 -175.3(10) . . . . ?
N1 C2 C3 C4 179.1(9) . . . . ?
N6 C2 C3 C4 2.1(11) . . . . ?
N1 C2 C3 C14 0.5(17) . . . . ?
N6 C2 C3 C14 -176.4(9) . . . . ?
C14 C3 C4 C8 -3(2) . . . 3_666 ?
C2 C3 C4 C8 179.1(11) . . . 3_666 ?
C14 C3 C4 C5 176.6(11) . . . . ?
C2 C3 C4 C5 -1.8(11) . . . . ?
C3 C4 C5 C8 -179.0(9) . . . . ?
C8 C4 C5 C8 0.2(16) 3_666 . . . ?
C3 C4 C5 N6 0.9(11) . . . . ?
C8 C4 C5 N6 -179.9(9) 3_666 . . . ?
N1 C2 N6 C5 -178.6(9) . . . . ?
C3 C2 N6 C5 -1.6(10) . . . . ?
N1 C2 N6 B7 3.5(15) . . . . ?
C3 C2 N6 B7 -179.5(9) . . . . ?
C8 C5 N6 C2 -179.6(10) . . . . ?
C4 C5 N6 C2 0.5(10) . . . . ?
C8 C5 N6 B7 -1.8(16) . . . . ?
C4 C5 N6 B7 178.3(9) . . . . ?
C2 N6 B7 F22 -128.8(10) . . . . ?
C5 N6 B7 F22 53.8(13) . . . . ?
C2 N6 B7 F21 108.4(10) . . . . ?
C5 N6 B7 F21 -69.1(13) . . . . ?
C2 N6 B7 N8 -10.2(12) . . . . ?
C5 N6 B7 N8 172.4(8) . . . . ?
F22 B7 N8 C13 135.4(9) . . . . ?
F21 B7 N8 C13 -106.1(10) . . . . ?
N6 B7 N8 C13 14.8(12) . . . . ?
F22 B7 N8 C9 -54.2(11) . . . . ?
F21 B7 N8 C9 64.2(11) . . . . ?
N6 B7 N8 C9 -174.8(8) . . . . ?
N6 C5 C8 C4 179.9(9) . . . 3_666 ?
C4 C5 C8 C4 -0.2(16) . . . 3_666 ?
C13 N8 C9 C10 -3.1(15) . . . . ?
B7 N8 C9 C10 -173.9(10) . . . . ?
N8 C9 C10 C11 4.2(17) . . . . ?
C9 C10 C11 C12 -4.8(18) . . . . ?
C10 C11 C12 O23 179.4(10) . . . . ?
C10 C11 C12 C13 4.3(17) . . . . ?
C9 N8 C13 N1 177.3(9) . . . . ?
B7 N8 C13 N1 -12.8(14) . . . . ?
C9 N8 C13 C12 2.6(14) . . . . ?
B7 N8 C13 C12 172.5(9) . . . . ?
C2 N1 C13 N8 3.6(15) . . . . ?
C2 N1 C13 C12 178.3(9) . . . . ?
C11 C12 C13 N8 -3.3(15) . . . . ?
O23 C12 C13 N8 -178.9(8) . . . . ?
C11 C12 C13 N1 -178.2(10) . . . . ?
O23 C12 C13 N1 6.2(13) . . . . ?
C4 C3 C14 C19B -22(3) . . . . ?
C2 C3 C14 C19B 156(2) . . . . ?
C4 C3 C14 C20A 27(2) . . . . ?
C2 C3 C14 C20A -155.3(18) . . . . ?
C4 C3 C14 C15B 158(2) . . . . ?
C2 C3 C14 C15B -24(2) . . . . ?
C4 C3 C14 C15A -155(3) . . . . ?
C2 C3 C14 C15A 24(3) . . . . ?
C19B C14 C15A C16A 35(4) . . . . ?
C20A C14 C15A C16A -7(4) . . . . ?
C15B C14 C15A C16A -80(3) . . . . ?
C3 C14 C15A C16A 174(3) . . . . ?
C18B C17 C16A C15A -48(4) . . . . ?
F20 C17 C16A C15A 177(3) . . . . ?
C16B C17 C16A C15A 72(4) . . . . ?
C19A C17 C16A C15A -9(5) . . . . ?
C14 C15A C16A C17 8(5) . . . . ?
C18B C17 C19A C20A 85(4) . . . . ?
F20 C17 C19A C20A -177(2) . . . . ?
C16A C17 C19A C20A 9(4) . . . . ?
C16B C17 C19A C20A -34(4) . . . . ?
C17 C19A C20A C14 -7(4) . . . . ?
C19B C14 C20A C19A -72(3) . . . . ?
C15B C14 C20A C19A 45(3) . . . . ?
C15A C14 C20A C19A 6(4) . . . . ?
C3 C14 C20A C19A -175(2) . . . . ?
C19B C14 C15B C16B -5(3) . . . . ?
C20A C14 C15B C16B -46(3) . . . . ?
C15A C14 C15B C16B 75(3) . . . . ?
C3 C14 C15B C16B 175(2) . . . . ?
C14 C15B C16B C17 8(4) . . . . ?
C18B C17 C16B C15B -6(5) . . . . ?
F20 C17 C16B C15B 176(2) . . . . ?
C16A C17 C16B C15B -84(4) . . . . ?
C19A C17 C16B C15B 33(4) . . . . ?
F20 C17 C18B C19B 179(3) . . . . ?
C16A C17 C18B C19B 43(5) . . . . ?
C16B C17 C18B C19B 1(6) . . . . ?
C19A C17 C18B C19B -77(4) . . . . ?
C20A C14 C19B C18B 76(4) . . . . ?
C15B C14 C19B C18B -0(4) . . . . ?
C15A C14 C19B C18B -41(4) . . . . ?
C3 C14 C19B C18B 180(3) . . . . ?
C17 C18B C19B C14 3(6) . . . . ?
C11 C12 O23 C24 7.5(15) . . . . ?
C13 C12 O23 C24 -177.2(8) . . . . ?
C12 O23 C24 C25 -176.1(9) . . . . ?
O23 C24 C25 C26 -64.3(13) . . . . ?
C24 C25 C26 C27 178.0(11) . . . . ?
C25 C26 C27 C28 -179.1(14) . . . . ?
C26 C27 C28 C29 178.4(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.166
_database_code_depnum_ccdc_archive 'CCDC 1003615'
